Benzyl Bromide → HCID 68753687, compound

HRID 333322

Reaction equation

HRID 333322 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>CN(C=O)C.O>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:30][C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[O:10])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 30824342(4-Biphenyl)propionic acid

Product 1

HCID 68753687HCID 68753687, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(biphenyl-4-yl)propanoic acid (5 g, 22.10 mmol) and K2CO3 (6.11 g, 44.2 mmol) in DMF (22 ml), BnBr (3.94 ml, 33.1 mmol) was added. After stirred for 15 hours, additional BnBr (3.94 ml, 33.1 mmol) was added. After stirred for further 22 hours, the reaction was diluted with H2O, extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was diluted with EtOAc (150 ml), and NH-silica gel was added to the suspension. The EtOAc was evaporated, and the resulted slurry was allowed to stir for 1 hour. The slurry was eluted with 10% EtOAc/heptane (150 ml) to give benzyl 3-(biphenyl-4-yl)propanoate (6.16 g); Retention time=1.71 minutes (condition A); 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (t, J=7.8 Hz, 2H) 3.01 (t, J=7.8 Hz, 2H) 5.12 (s, 2H) 7.21-7.47 (m, 14H).

Workup

  1. additionwas added
  2. stirringAfter stirred for further 22 hours
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe obtained residue was diluted with EtOAc (150 ml), and NH-silica gel
  9. additionwas added to the suspension
  10. customThe EtOAc was evaporated
  11. stirringto stir for 1 hour
  12. washThe slurry was eluted with 10% EtOAc/heptane (150 ml)

Sources & evidence

ORD record
ord-b78513581fb14ee78dd3ce13c4628a39
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Linked notes

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